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Questions to Ask Before Hiring an AI Agency

Twenty minutes of the right questions will save you months of the wrong contract.

AR
AgencyRadar Team
2026-03-21 · 5 min read

Why Most Evaluations Go Wrong

Most buyers evaluate AI agencies by looking at their website, reading a case study, and watching a demo. None of those tell you what it's actually like to work with them under pressure, when requirements change, or when something breaks in production. These questions do.

Questions About Their Work

"Can you show me a live deployment similar to what we need?" — Not a demo they built for prospects. A real client's live chatbot or automation you can actually use.

"What went wrong on your last complex project, and how did you handle it?" — Agencies that have never had a project go sideways either haven't done enough projects or aren't being honest. How they handle problems is what matters.

"Who specifically will work on our project?" — You want to know if the senior person who pitched you will actually do the work or hand it to a junior.

Questions About Process

"What does your change order process look like?" — If they don't have one, scope creep will be your problem.

"How do you handle a requirement that turns out to be more complex than scoped?" — Their answer tells you if they're transparent or if they'll silently cut corners.

"What does handoff look like? What documentation do we get?" — After launch, can your team maintain what they built, or are you dependent on them forever?

Questions About Their Business

"How many active client projects do you have right now?" — A team of 3 with 20 active projects will miss your deadlines.

"What's your client retention rate?" — Agencies with happy clients have high retention. This is hard to fake.

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